Category: 4277-34-3

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4277-34-3, name is Cyclooct-4-enol, molecular formula is C8H14O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of Cyclooct-4-enol

Synthesis of Cer-TCO (FIG. 7) (0139) Cis-1,5-cyclooctadiene 1 was converted to cyclooctene monoepoxide 2 with m-CPBA (Clark, et al., 2010, J. Am. Chem. Soc. 132:3405-3412). The monoepoxide was reduced with LiAlH4 to the alcohol 3 (Clark, et al., 2010, J. Am. Chem. Soc. 132:3405-3412). Cis-cyclooctenol 3 was isomerized to trans-cyclooctenol 4 according to Royzen, et al., 2008, J. Am. Chem. Soc. 130:3760-3761. From TCO 4 the corresponding p-nitrophenol carbonate 5 was prepared (Liu, et al., 2012, J. Am. Chem. Soc. 134:792-795).

With the rapid development of chemical substances, we look forward to future research findings about 4277-34-3.

Reference:
Patent; Yale University; ERDMANN, Roman; SHRADER, Alanna Schepartz; TOOMRE, Derek; (34 pag.)US2016/115180; (2016); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.4277-34-3, name is Cyclooct-4-enol, molecular formula is C8H14O, molecular weight is 126.2, as common compound, the synthetic route is as follows.Computed Properties of C8H14O

Compound AA8. A mixture of (Z)-cyclooct-4-en-1-ol (42 mg, 330 mumol, 1.5 eq.), N,N?-disuccinimidyl carbonate (DSC) (101 mg, 396 mumol, 1.8 eq.), and TEA (40 mg, 396 mumol, 1.8 eq.) in MeCN (0.5 mL) was degassed and purged with N2 for 3 times. After stirred at 25 C for 4 h under N2, the mixture was added into a mixture of compound AA7 (91.98 mg, 220 mumol, 1 eq.) and TEA (40 mg, 396 mumol, 1.8 eq.) in DMF (0.5 mL) dropwise at 25 C under N2. After stirred at 25 C for 0.5 h under N2, the reaction mixture was filtered and the filtrate was concentrated in vacuo. The mixture was purificated by prep-HPLC (HCl) to afford compound AA8 (8.9 mg, 16 mumol, 7% yield) as a yellow oil. 1H NMR (CD3OD, 400 MHz) delta 8.47 (br s, 1H), 8.42 (s, 1H), 5.75-5.50 (m, 2H), 4.70 (br s, 1H), 4.15-4.00 (m, 1H), 3.96 (s, 3H), 3.29-3.18 (m, 4H), 3.14-2.97 (m, 2H), 2.62-2.49 (m, 2H), 2.44-2.32 (m, 1H), 2.25 (br d, J = 13.2 Hz, 2H), 2.21-2.13 (m, 2H), 2.10-2.00 (m, 1H), 1.95-1.81 (m, 4H), 1.73 (br dd, J = 4.6, 9.9 Hz, 1H), 1.68-1.34 (m, 7H), 1.10 (br s, 1H), 0.54 (br d, J = 7.3 Hz, 2H), 0.30 (br s, 1H).33

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4277-34-3, Cyclooct-4-enol, and friends who are interested can also refer to it.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
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Synthetic Route of 4277-34-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4277-34-3 as follows.

General procedure: A ?10 g? Biotage SNAP cartridge wrapped in aluminum foil was used to house the modified silica gel (13.2 g). The (Z)-cyclooctene derivative (0.012-0.024 M in solvent) and methyl benzoate (2.0 equiv) were dissolved in the indicated solvent in a quartz flask. After sparging the contents with N2 for 15 minutes, the flask was placed in a Rayonet reactor and connected via PTFE tubing to a column (Biotage SNAP) and an FMI pump. The column was then packed with silver nitrate exchanged sulfonated silica gel. Any remaining space between the silica and the cartridge cap was filled with cotton. The column was flushed with the reaction solvent, followed by equilibration via circulation with the FMI pump (ca. 100 mL per minute). The solution in the quartz flask was then irradiated at 254 nm under continuous flow for the indicated time. The SNAP cartridge was washed with additional solvent, and then dried with a stream of compressed air. A solution of NH3-saturated MeOH was allowed to pass through the column and the effluent was collected until no more trans-cyclooctene product was detected by TLC. The collected solution was then concentrated by rotary evaporation and the residue was purified by flash silica gel chromatography to obtain pure trans-cyclooctenes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4277-34-3, its application will become more common.

Reference:
Article; Darko, Ampofo; Boyd, Samantha J.; Fox, Joseph M.; Synthesis; vol. 50; 24; (2018); p. 4875 – 4882;,
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Related Products of 4277-34-3, Adding some certain compound to certain chemical reactions, such as: 4277-34-3, name is Cyclooct-4-enol,molecular formula is C8H14O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4277-34-3.

(Z)-Cyclooct-4-enol (2.0 g, 15.8 mmol) was added slowly to a suspension of sodium hydride (1.3 g of 60% dispersion in mineral oil, 31.7 mmol) in 50 mL THF. This was stirred at reflux for 1 hour, then a solution of iodoacetic acid (2.9 g, 15.8 mmol) in 10 mL THF was added and reflux was continued for 4 hours, then the reaction was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in 10% NaOH(aq) (50 mL) and extracted with Et2O (2×25 mL). The pH of the aqueous solution was lowered to (4) by the addition of 6N HCl and extracted again with DCM (2×25 mL). Separately, the organic solutions were dried (MgSO4), filtered, and concentrated by rotary evaporator. The ether extraction resulted in 1.0 g of starting (Z)-cyclooct-4-enol and the DCM extraction resulted in 1.9 g of (Z)-2-cyclooct-4-enyloxy)acetic acid (2) (65.5% yield).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 4277-34-3, Cyclooct-4-enol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; Reiner, Thomas; Keliher, Edmund J.; Weissleder, Ralph; US2013/309170; (2013); A1;,
Alcohol – Wikipedia,
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Electric Literature of 4277-34-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4277-34-3 as follows.

(E)-2-Cyanoethyl cyclooct-4-enyl diisopropylphosphoramidite (2). To a solution of (E)-Cyclooct-4-enol (70 mg, 0.56 mmol) in 2 ml of absolute CH2Cl2 under argon diisopropylethylamine (0.33 ml, 1.90 mmol) was added. The mixture was cooled to 0C and 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite (141 mul, 0.63 mmol, 1.05 eq) was added. After stirring for one hour at RT, the reaction mixture was directly loaded on a silica column. Purification by flash chromatography (hexane/ethyl acetate 95:5) yielded the product as colourless oil (100 mg, 0.31 mmol, 55%). 1H-NMR (500 MHz, CDCl3, 25C, TMS): delta = 1.16-1.19 (m, 12H), 1.55-1.63 (m, 2H), 1.86-2.37 (m, 8H), 2.63 (t, J = 6.55 Hz, 2H), 3.51-3.61 (m, 3H), 3.72-3.85 (m, 2H), 5.38-5.44 (m, 1 H), 5.54-5.61 (m, 1H). 13C {1H, 31P} NMR (75 MHz, CDCl3, 25C, TMS): delta=20.3, 24.4, 24.6, 31.1, 31.3, 32.7, 32.8, 34.4, 40.0, 40.3, 42.9, 43.0, 43.2, 58.1, 58.3, 79.6, 80.0, 117.6, 132.6, 135.1, 135.2. 31P-NMR (121 MHz, CDCl3,25C, H3PO4): delta=145.5, 146.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4277-34-3, its application will become more common.

Reference:
Patent; Deutsches Krebsforschungszentrum; Ruprecht-Karls-Universitaet Heidelberg; Schoch, Juliane; Jaeschke Andres; Samanta, Ayan; Wiessler, Manfred; EP2565199; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts